Hydrochloric Acid → 4-Hydroxy-4'-octylazobenzene

HRID 867355Notes

Reaction equation

HRID 867355 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.[N:17]([O-])=O.[Na+].[OH-].[Na+].[C:23]1([OH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[OH:29][C:23]1[CH:28]=[CH:27][C:26]([N:17]=[N:13][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 996PhenolHCID 14798Sodium HydroxideHCID 853464-OctylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27534414-Hydroxy-4'-octylazobenzeneYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

35 g (0.17M) of 4-octylaniline was cooled to 0° C. or below, 85 g of10% aqueous hydrochloride acid solution was added, and then a solution of 12.0 g of sodium nitrite in 68 ml of water was added. During the addition,the mixture was cooled so as not to exceed 0° C. After the addition,the mixture was allowed to react for 30 minutes, transferred into a dropping funnel and added dropwise into 170 g of an 8% NaOH aqueous solution containing 16 g of phenol held at 5° C. or below. After the addition, the mixture was stirred for 1 hour, and then 10% hydrochloric acid aqueous solution was added thereto until a pH of 5-6 to precipitate the reaction product. The precipitate was separated by filtration, washed with water, overnight under reduced pressure. After thedrying, the product was washed with 500 ml of petroleum ether and further dried under reduced pressure to obtain 30.8 g (0.10M) of 4-hydroxy-4'-octylazobenzene. The yield was 59%.

Workup

  1. temperatureDuring the addition,the mixture was cooled so as not
  2. customto exceed 0° C
  3. customto react for 30 minutes
  4. customtransferred into a dropping funnel
  5. customheld at 5° C. or below
  6. additionAfter the addition
  7. customuntil a pH of 5-6 to precipitate the reaction product
  8. customThe precipitate was separated by filtration
  9. washwashed with water, overnight under reduced pressure
  10. washAfter thedrying, the product was washed with 500 ml of petroleum ether
  11. customfurther dried under reduced pressure

Sources & evidence

ORD record
ord-48c5f6c941884a6bb9f7f56123956239
Source dataset
uspto-grants-1988_10
Patent number
US04775223

Reaction notes

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